Lena, 29, works in HR for a tech company in San Francisco and enjoys her job. She works decent hours, likes her colleagues, and gets paid well for what she does (yes, she’s done her research and knows that her salary is commensurate with her market value). However, she lives in an expensive city, only recently finished paying off her student loans, and could certainly stand to have some extra cash. Yes, she could probably stand to spend less, but instead of that, what about making more?
None of her friends have second jobs, so the idea seems unorthodox, but she has many interests outside of her office, and it seem like an additional source of income to supplement her salary would be a great thing. For example, she sometimes helps her friends with their résumés, and has considered starting a side gig as a résumé consultant. She also speaks fluent Italian, and thinks about giving private Italian lessons (she’d love to practice more). Is this nutty? Or, even worse, will working in her spare time make her burn out and interfere with her success at her regular job? Will her employer take this as a sign that she’s less committed to the company? Or is it just a great way to improve her finances?
We are a culture that loves to believe everyone should find one thing at which they are exceptionally good. If you pinpoint that thing, hurl yourself at it, kick and struggle, and give up some sleep (but not too much, because that thing also needs a rested brain); then money will eventually appear, drawn by the tidal pull of your talent and drive. And if it doesn’t, you’ll be so overwhelmingly fulfilled by your calling that you won’t even notice — maybe.
For the rest of us, there’s moderation. The majority of people on this earth are not geniuses in one particular area, or the brains behind a singular industry-shifting idea; instead, we’re pretty good at a couple of things, and quite good if we work hard at them. Maybe it’s smart to pick just one (in your case, Lena, you could become the HR guru of the San Francisco tech world), but you could also pay attention to the fact that you are a human with multiple talents and areas of interest, and you are welcome to develop and monetize as many as you want, within reason. That’s the beauty of a side hustle — ideally, it’s a hobby you get paid for.
Lena, your reservations speak to widely held societal notions that diversifying your income streams might mean you don’t take your primary career seriously. Having more than one job is often associated with slashes— waiter-slash-actors, nanny-slash-novelists, and other people who wish they could be doing just one of their slash-jobs full time but haven’t “made it” enough to do so and still afford rent. This isn’t your situation; you’re not going to quit your HR job as soon as your Italian tutoring business gets off the ground. A side gig is the dessert course of your income — nice to have, but not essential, nor the main event. Remember the difference.
“I personally think that one of the greatest fallacies in our education system is the idea that we’re supposed to find our one true passion and pursue it for 40-plus years,” says Gabrielle Bill, a career adviser at SoFi, a company that offers personal-finance services online. “Most people have more than one passion, and those passions don’t always quite align in the form of a single career. A mathematician might have a huge love of painting, or a nurse might love to sing. Side hustles allow us to tap into our passions in a way that can generate some extra income while allowing us to pay the bills and fulfill ourselves more completely.”
But how do you know when to let a hobby stay a hobby, and when to try your hand at making a few bucks off of it? For starters, look at the things you do well when others aren’t watching. “Get creative with what you do naturally,” says Jen Sincero, the author of You Are a Badass at Making Money: Mastering the Mindset of Wealth, a cheerful manifesto on removing obstacles between yourself and the income of your dreams (or, as Sincero puts it, “helping people find ways to make assloads of cash doing what they love and not working all the time.”) “We often don’t value what comes naturally to us because we think that everyone must have those abilities,” she continues. “For example, I have a friend who’s amazing at organizing. She’s so type-A and tidy and anal retentive, and she can come in and completely change my life by tearing through my closet for a few hours. You can make a couple hundred bucks by doing something like that! Don’t take those talents for granted, and realize that other people will pay you for them.”
Remember, though, not all hobbies are fair game. “If the point of an activity is to be relaxing, changing that point to money isn’t a great idea,” says Sincero. “Then you have to show up for it differently, and that can take the fun out of it, absolutely. I’m a big fan of turning your hobbies into businesses, but not if it’s the hobby you do to relax and unplug.” There’s a lot of gray area here, so embrace the trial-and-error period. You might love knitting hats for your friends, but as soon as you begin taking orders on Etsy, your living room begins to feel like a sweatshop. Start slow.
Next, figure out how much you’ll charge, and don’t skimp, no matter how much you enjoy said activity. Maybe teaching Italian is so delightful that taking someone’s money for it feels like stealing gelato from a baby, but it’s better for everyone if you price appropriately. Charge too much, and you won’t get business; charge too little, and you might lose steam. “See it as an opportunity to do some mental work around your right to be paid,” says Sincero. “Reframe it so that you’re not taking money from somebody, but you’re exchanging a very valuable service that they’re happy to pay for. Thing of it in terms of what you’re giving to them.”
One of the things you’re giving is time, which brings up a third point: Do you have enough of it? “A side hustle transitions from an enriching experience to a depleting one when you’re working so many hours that you don’t have time to pursue other value-add aspects of your life,” says Bill. “If you find yourself exhausted at the end of the day in a bad way, unable to sleep because your mind is racing with all the things you have to do, or if your passion project starts to feel more like a chore, it might be time to reassess.” Of course, if you’re spread so thin that it’s affecting your performance at the job that delivers your primary income, then you’ll risk hurting your long-term financial health as well (and run yourself ragged, to boot).
Done properly, though, a second job won’t just bring in extra cash — it could even make you better at your primary career. Bill is a walking example: Although she currently has one full-time job, she previously had several concurrent gigs (including teaching, marketing, and career coaching). “Admittedly, it got stressful at times, but the variety of experiences fueled me,” she says. “I tapped into different parts of my brain, made amazing connections, and got to learn an exponential amount about time management, coaching different audiences, and juggling priorities. Ultimately I think the diversity of experience made me a more attractive candidate and showcased the breadth of hard and soft skills I can offer an employer.” Now, she actively looks to hire people who have juggled more than one thing at a time. “I see people with side hustles as better employees because I know they’re exercising some form of self-care,” she says. “If they are tapping into their passions, they’ll bring more of their whole selves to the job I’m recruiting for, rather than feeling like parts of them are stifled.”
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